Stereocontrolled total synthesis of amphidinolide X via a silicon-tethered metathesis reaction.
Two esterifications and an RCM to create the challenging trisubstituted C12-C13 double bond were required in the total synthesis of amphidinolide X (1) reported here. Assembling the three fragments in this order, no RCM occurred or the process yielded mainly isomer Z. However, generating the E double bond first, by a new variant of a Si-tethered metathesis (using Schrock's catalyst), and carrying out the esterification and macrolactonization steps later, 1 was obtained exclusively.
Rodríguez-Escrich
Carles
C
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Barcelona, Catalonia, Spain.
Urpí
Fèlix
F
Vilarrasa
Jaume
J
D007783:Lactones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D000097442:Amphidinolides
D007783:Lactones; D018942:Macrolides; D012825:Silicon; C480942:amphidinolide X; D000097442:Amphidinolides